2-[(2,5-Dimethoxyphenyl)methyl]oxirane | 1026729-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2,5-Dimethoxyphenyl)methyl]oxirane
• CAS: 1026729-16-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: YRZOAJFPWKSMIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2,5-Dimethoxyphenyl)methyl]oxirane 、 methyl 2-(acetoxy(4-methylphenyl)methyl)acrylate 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到(3E)-5-(2,5-二甲氧基苄基)-3-(4-甲基亚苄基)四氢-2H-吡喃-2-酮
  参考文献：
  名称：

  Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones

  摘要：

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.

  DOI：

  10.1021/jo800049p
• 作为产物：
  描述：

  2-烯丙基-1,4-二甲氧基苯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-[(2,5-Dimethoxyphenyl)methyl]oxirane
  参考文献：
  名称：

  First asymmetric total synthesis of novel and cytotoxic 2′-R-hydroxylanneaquinol

  摘要：

  A novel cytotoxic alkylated hydroquinone 2'-R-hydroxylanneaquinol (1), isolated from the organic extract of the plant Lannea welwitschii, has been synthesized for the first time using commercially available 4-methoxyphenol. The key step of this process involves the kinetic resolution of epoxide 6 using Jacobsen's reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.076

文献信息

• Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (<i>E</i>)- and (<i>Z</i>)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones
  作者：Samir K. Mandal、Moumita Paira、Subhas C. Roy

  DOI：10.1021/jo800049p

  日期：2008.5.1

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.
• First asymmetric total synthesis of novel and cytotoxic 2′-R-hydroxylanneaquinol
  作者：V. Suresh、K. Rajesh、J. Jon Paul Selvam、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2008.09.076

  日期：2008.12

  A novel cytotoxic alkylated hydroquinone 2'-R-hydroxylanneaquinol (1), isolated from the organic extract of the plant Lannea welwitschii, has been synthesized for the first time using commercially available 4-methoxyphenol. The key step of this process involves the kinetic resolution of epoxide 6 using Jacobsen's reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.